Azo dyestuffs and their production.



. of the benzene and napththalene series with r "ran snares earner orrion 'IAEVINSTEIN AND "JAMES BADDILEY, OYF BLACKLEY, MANCHESTER, ENG ILA-N13,. WSIG-NOm T LEVINSTEIN, LIMITED, OF BLACKLEY, MANGHEEJ'IER, ENGLAND, A TLIMITEDLIABILITY COMPANY.

A 'DYEST'D'FFS AND TEENS, PRODUCTIGN.

No Drawing.

,an Ireland, and both residents of Blackley, Manchester, in the county of Lancaster,

England, have invented new and useful New Azo Dyestuffs and Their Production, of which the following is a specification.

'Fhje invention relates to the roduction of new mono and disazo dyestu- 's and consists in combining diazo or diazoazo bodies the new azo dyestufl' components produced by combining brom- 'or chlor-acetylc'hlorid with an aminonaphthol sulfonic acid which does not contain the amino group in the 'ortho position to the hydroxyl group, and

-i with a rimary aromaticamino body. When the by roxyl group is in the alpha position the peri position is equivalent to the ortho position and must reihahl unoccupied by the amino group, and any reference hereinafter to the amino grou not being in the ortho position to the-11y 'oxyl group is intended also to include a reference to the peri position when the l'iyidro'xyl group is in the alpha position.

. The dyestufi components may :be produced in two series, according to whether the amino-napliithel-sulfon ic acid or the primary aromatic amino body, is first combined with -the halogen acety-lchlorid. These two series [have the follow-inggeneral formula where Xf may represent hydrogen or a sulfonic group in the naphthalene nucleus and .R the residue ofthe primary aromatic amin.

The following examples will serve to illustrate how our-invention may be carried into effect, but wedo not confine ourselves to the Example 1: 233 parts of 2.6 naphthylamin sulfonic acid are diazotized by means Specification of Letters Patent.

Application filed May 20, 1912. Serial lie-698,492.

Patented Apr. M, rain.

of 69 parts of sodium nitrite and the requisite amount of hydrochloric'acid, and the diazo compound thus obtained is combined with 3T2 parts of 2-phenylaminoacetylamino- 5-naphthol-7-sulfonic acid having the con stitution C10H,(SO3H) on .nnooou nnc n .paraxyliclin. The intermediate product thus formed is isolated by salting out from the solution made mineral acid with hydrochloric acid, transformed into its sodium salt, and rediazotized by means of 69 parts of sodium nitrite and the necessary amount of hydrochloric acid. The diazoazo compound is then combined with 372 parts of the anilid of Q-aminb-5-naphthol-7-sulfonic acid glycin having the constitution o n, son (on .nuomoonnlo u in the presence of an excess 0]": sodium carbonate. The resulting: dystuff is isolated in the usual Way. It dyes unmordanted cotton in reddishviolet shades of good fastness to acids, al'k-ailis, and light.

Exampleli: 223 parts of Q-naphthylamin- 6-sulfonic acid are diazotized as in Example 1, and combined in the presence of an excess of sodium carbonate with 417 parts of Q-metanitrQphenylaminoacetylamino'5-naphthol-T-sulfonic acid of the following constitution When the combination is completed the solution is heated up and the dyestufi' salted out. It dyes cotton in very bright'yellowislLred shades of great fastness to acids and good fastness to light.

The nitro group in the above coloring matter is capable of undergoing reduction,

and when :the dyestufi' is acted upon by sodium sulfid in anaqueous solution, a new compound 'isformed', which dyes unmordanted cotton in fiery yellowish red shades of excellent fast-ness to acids.

Example 4: 277' parts of aininazobenzol sulfonic acid are diazotized by means of 69 parts of sodium nitrite and thewrequisite amount of hy 'rochloric acid in the ordidium carbonate.

nary way. Tlis diazo compound is then combined with 372 arts of 2-phenylaminoacetylamino-5-napht ol-7-sulfonic acid of the formula given in Example 1 dissolved in water in the-presence of sufficient sodium carbonate to keep the solution alkaline. The resulting dyestufi is salted-out in the usual way. It dyes unmordanted cotton in red shades of good fastness to acids, and alkalis, and of great fastness to light.

If in the place. of' the 2-phenyla'minoacetylamino-5-naphthol-7-sulfonic acid in in the presence of a suitable excess of so When combination is completed the color is isolated inthe usual way. It dyes wool in dark brown black'kshades,

, which on afterchroming become dark olive. The afterchromed shades are extremely fast to light, milling and potting.

Example 6: 154 parts of l-nitro-Q-amino phenol are diazotized by means of 69 parts of sodium nitrite and the necessary amount of hydrochloric acid and the resulting diazo compound is combined with 452 parts of the meta-su'lfo-anilid of the glycin of 2-amino- 'S-naphthoLG-sulfonic acid having the constitution' omnNnecnaconn fsosn in the presence of an excess of sodium carbonate. VVhenicombination is completed dyeswool in brown shades which on afterchroming become brown-black and exceedingly fast to light, milling, and potting.

What we claim is i 1. The production of azo dyestufis by combining a diazo body of 'the' aromatic series with the component produced by combining halogenacetylchlorid, a primary arosulfonic acidwhich' does not contain the amino group' in the ortho position to the hydroxyl group, substantially as herein set forth.

. 2. An azo dyestufi having the general formula y 2;: cwHs-Nn.co.cHiNnR y-NTii where 1?. indicates a number less than 3, R the residue of a primary aromatic ami'n which has been diazotized and coupled with the new component.

"In witness whereof we have hereunto set ing witnesses.

HERBERT LEVINSTE'IN. JAMES BADDILEY. Witnesses: I

WILnIAM 'Gno. Hers, ERNOLD SIMPSON Mosnnnr.

the dyestufi is isolated'in the usual way. "It' matic amino body, and an amino-naphthob amii. and Y the residue of the aromatic our hands in the presence of two subscrih; 

